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CAS No. : | 15016-43-0 | MDL No. : | MFCD01074679 |
Formula : | C8H9BO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SYBQEKBVWDPVJM-UHFFFAOYSA-N |
M.W : | 147.97 | Pubchem ID : | 4366886 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.36 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.6 |
Log Po/w (WLOGP) : | -0.1 |
Log Po/w (MLOGP) : | 0.85 |
Log Po/w (SILICOS-IT) : | 0.01 |
Consensus Log Po/w : | 0.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.04 |
Solubility : | 1.36 mg/ml ; 0.00918 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.06 |
Solubility : | 1.29 mg/ml ; 0.00869 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.71 |
Solubility : | 2.86 mg/ml ; 0.0193 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.0 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In tetrahydrofuran; | EXAMPLE 2 Preparation of 2-(3-vinyl-phenyl)pyridine The reaction was performed with <strong>[15016-43-0]3-vinyl-phenylboronic acid</strong> (10 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and tetrakis(triphenylphosphine) palladium (Pd(Ph3)4, 0.06 g, 1 mol %) according to Example 1. The yield was 80%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | 2-Amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one (Scheme 9, D); A thick-walled glass vial was charged with a stir bar, 2-arnino-6-(3-bromo-benzyl)-3-methyl-3H-pyrimidin-4-one (Scheme 9, C) (120 mg, 0.2 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (46 mg, 0.39 mmol), dichlorobis(triphenylphosphine)-palladium (II) (approximately 6 mg, 0.006 mmol), Cs2C03 (246 mg, 0.76 mmol) and DME/H20/EtOH (7:3:2; 5 mL). The vial was crimp sealed and subjected to microwave radiation for 5 min at 150 C. The resultant black slurry was filtered, washed with methanol (3x3 mL) then concentrated in vacuo. The resultant residue was then purified by reverse phase HPLC. Appropriate fractions were concentrated via centrifugal evaporation to afford the white trifluoroacetic acid salt of the title compound (62 mg, 35%). *H NMR (300 MHz, DMSO-^/TFA-d) 5 3.27 (s, 3H), 3.93 (s, 2H), 5.33 (d, J = 11.0 Hz, 1H), 5.93 (d, J = 17.7 Hz, 1H), 5.98 (s, 1H), 6.83 (dd, J = 17.7, 11.0 Hz, 1H), 7.36 - 7.52 (m, 4H), 7.59 (d, J = 16.8 Hz, 1H), 7.62 (d, J = 17.2 Hz, 1H), 7.72 - 7.73 (m, 2H); m/z (APCI+) M+l = 318.2; fe = 2.17 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.0833333h;Microwave irradiation; | 2-Amino-3-methyl-6-(3'-vinyl-biphenyl-3-ylmethyl)-3H-pyrimidin-4-one (Scheme 9, D); A thick-walled glass vial was charged with a stir bar, 2-amino-6-(3-bromo-benzyl)-3-methyl-3H-pyrimidin-4-one (Scheme 9, C) (120 mg, 0.2 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (46 mg, 0.39 mmol), dichlorobis(triphenylphosphine)-palladium (II) (approximately 6 mg, 0.006 mmol), Cs2CO3 (246 mg, 0.76 mmol) and DME/H2O/EtOH (7:3:2; 5 mL). The vial was crimp sealed and subjected to microwave radiation for 5 min at 150 0C. The resultant black slurry was filtered, washed with methanol (3 x 3 mL) then concentrated in vacuo. The resultant residue was then purified by reverse phase HPLC. Appropriate fractions were concentrated via centrifugal evaporation to afford the white trifluoroacetic acid salt of the title compound (62 mg, 35%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: To a mixture of 1 (0.21 g, 0.5 mmol), 2aeo (2.0 mmol), palladium catalyst [tetrakis(triphenylphosphine)] in an argon flushed pressure tubewas added THF (5 ml) and aqueous K2CO3 (2 ml, 2 M). The reaction mixture was refluxed for 12 h and was allowed to cool down to room temperature and then cold water (8 ml) was added. After stirring for additional 15 min, the mixture was extracted with dichloromethane (3 20 ml). The organic layer was washed with brine, dried over anhyd Na2SO4, filtered and concentrated in vacuo to give an inseparable 1:1 mixture of 3a-o and of the corresponding 2,3,5,6-tetraaryl-p-dihydrobenzoquinone. The mixture was treated with DDQ (0.85 mmol) in benzene (8.5 ml) and was stirred at room temperature for 3 h. The reaction mixture was filtered, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes/EtOAc¼9:1) to give products 3a-o. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 12h;Inert atmosphere; | General procedure: To a mixture of 1 (0.21 g, 0.5 mmol), 2aeo (2.0 mmol), palladium catalyst [tetrakis(triphenylphosphine)] in an argon flushed pressure tubewas added THF (5 ml) and aqueous K2CO3 (2 ml, 2 M). The reaction mixture was refluxed for 12 h and was allowed to cool down to room temperature and then cold water (8 ml) was added. After stirring for additional 15 min, the mixture was extracted with dichloromethane (3 20 ml). The organic layer was washed with brine, dried over anhyd Na2SO4, filtered and concentrated in vacuo to give an inseparable 1:1 mixture of 3a-o and of the corresponding 2,3,5,6-tetraaryl-p-dihydrobenzoquinone. The mixture was treated with DDQ (0.85 mmol) in benzene (8.5 ml) and was stirred at room temperature for 3 h. The reaction mixture was filtered, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes/EtOAc¼9:1) to give products 3a-o. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 80℃;Inert atmosphere; | b) Preparation of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propyl-3'-vinylbiphenyl; To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenyl trifluoromethanesulfonate (238 mg, 497 mumol) in 1,4-dioxan, potassium phosphate (401 mg), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (88 mg), and tetrakis triphenylphosphine palladium complex (57 mg) were added at room temperature under an argon atmosphere, and the resultant mixture was heated at 80 C. After completion of the reaction, the reaction solution was neutralized by adding water and 2 mol/L of hydrochloric acid, extracted with ethyl aceate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and the title compound (175 mg, yield 81%) was obtained as a colorless oil.1H-NMR (CDCl3) delta: 0.82 (3H, t, J=7.3 Hz), 1.53-1.64 (2H, m), 2.57 (2H, t, J=7.6 Hz), 3.58 (3H, s), 4.89 (2H, s), 5.30 (1H, dd, J=0.5, 10.8 Hz), 5.76 (1H, dd, J=0.5, 17.6 Hz), 6.70 (1H, dd, J=10.8, 17.6 Hz), 6.30-7.55 (7H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;Pd(PPh3)3; In 1,2-dimethoxyethane; nitrogen; water; ethyl acetate; | Step 1 A solution of 1,3-dibromobenzene (5.3 mL, 43.9 mmol), potassium carbonate (14.0 g, 101 mmol) and <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (5 g, 33.8 mmol) in DME (100 mL) and water (20 mL) (in a pressure vessel) was sparged with nitrogen for 15 min. Pd(PPh3)3 (1.17 g, 1.014 mmol) was added and then the reaction was heated to 80 C. overnight. The reaction was cooled to r.t. and evaporated on the rotovap. The residue was diluted in EtOAc and washed with water then brine, dried over MgSO4, filtered and evaporated to give the crude material. The crude material was purified by flash chromatography on the Biotage (0-5% EtOAc:Hex) to give 3-bromo-3'-vinylbiphenyl (5.21 g, 20.10 mmol, 60% yield) as a clear liquid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 5.33 (d, J=10.79 Hz, 1H) 5.84 (dd, J=17.57, 0.75 Hz, 1H) 6.80 (dd, J=17.57, 10.79 Hz, 1H) 7.32 (t, J=7.78 Hz, 1H) 7.38-7.48 (m, 3H) 7.51 (dddd, J=13.24, 7.84, 1.76, 1.00 Hz, 2H) 7.56-7.61 (m, 1H) 7.76 (t, J=1.88 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 70℃; for 8h;Inert atmosphere; | General procedure: The reaction was carried out in a pressure tube. To a dioxane suspension (5 mL) of the <strong>[7657-09-2]1,4-dibromo-2-(trifluoromethyl)benzene</strong> (6), Pd(PPh3)4 (3-5 mol%) and of the arylboronic acid (2) was added an aqueous solution of K2CO3 (2 M, 1-2 mL). The mixture was heated at the indicated temperature (70 8C) under Argon atmosphere for the indicated period of time (8 h). The solution was cooled to 20 C, poured into H2O and CH2Cl2 (5 mL each), and the organic and the aqueous layers were separated. The later was extracted with CH2Cl2 (3 15 mL). The combined organic layers were washed with H2O (3 10 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography (flash silica gel, heptanes/EtOAc) to give 4-bromo-3-(trifluoromethyl)biphenyls (7a-o) (79-94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With magnesium sulfate; In tetrahydrofuran; at 20℃; for 2h; | General procedure: 4,4,5,5-Tetramethyl-2-(4-vinylphenyl)-1,3,2-dioxaborolane 4a. 3a (1.00 g, 6.76 mmol), pinacol (802 mg, 6.80 mmol) and two spatula tips of magnesium sulphate were combined in anhydrous THF (50 mL) and left to stir at room temperature for 2 h. The mixture was filtered and concentrated under reduced pressure to afford 1.55 g of the pure expected product as a colourless liquid in quantitative yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 90℃; for 2h;Product distribution / selectivity; | Step 2: (R)-4-( 1 -cyclopropylethylamino)-6-(3 -vinylphenyl)pyrrolo[ 1 ,2-b]pyridazine- 3-carboxamide[00276] To a degassed solution of (R)-6-bromo-4-(l- cyclopropylethylamino)pyrrolo [l,2-b]pyridazine-3-carboxamide (100 mg, 0.309 mmol), <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (137 mg, 0.928 mmol) and K2CO3 (0.464 mL, 0.928 mmol) in DME (Volume: 2 mL) was added Pd(Ph3P)4 (21.45 mg, 0.019 mmol). The reaction mixture was heated to 90 C for 2 hrs. The reaction mixture was diluted with 10 mL of EtOAc and then washed with 5 mL of water and 5 mL of brine. The organic phase was concentrated to yield a crude product which was purified on prep silica gel TLC plate with hexanes/EtOAc(2/l) to yield a product. It was triturated in MeOH. The solid was collected as the desired product (79.7 mg, 74% yield). MS (ES+) m/z: 347.3 (M+H); HPLC: 86%, retention time: 3.808 min (analytical HPLC Method B). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In ethanol; water; toluene; for 1h;Reflux; | General procedure: To a solution of bromide 4 (52.8 mg, 0.15 mmol) and 4-(methoxycarbonyl)phenylboronic acid (32.4 mg, 0.18 mmol) in a mixture of toluene (1.5 mL), EtOH (0.9 mL) and 1 M aq K2CO3 (1.5 mL) was added Pd(PPh3)4 (6.9 mg, 4 mol %) and PdCl2(dppf)·CH2Cl2 (3.7 mg, 3 mol %). After being stirred under reflux for 1 h, the mixture was extracted with CHCl3. The organic layers were dried over MgSO4 and concentrated. The residue was purified by flash chromatography over aluminum oxide with n-hexane/EtOAc (10:0/9:1) to give the compound 5a as colorless solid (47.3 mg, 77%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [bmpy]2[PdCl4]; In N,N-dimethyl-formamide; at 130℃; for 3h;Microwave irradiation; | General procedure: The oxidative Heck reaction was carried out in a 50 mL Schlenk tube. The solid substrates: phenylboronic acid (1.5 mmol, 0.184 g) and palladium complex (0.02 mmol) were weighted and placed in the Schlenk tube which was evacuated and filled with oxygen. Next,olefin (1 mmol) and 5 mL of the solvent saturated with oxygen (30 min) were added with a pipette in the atmosphere of oxy-gen. The reactor was closed with a rubber plug and the reaction mixture was stirred in 130C. After the given reaction time, the reactor was cooled down and the organic products were extracted with 20 mL of diethyl ether. For better phase separation 1 mL of water was added; 0.15 mL of mesitylene was added as an internal standard. The organic products were analyzed using the GC-MS method. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 60℃; for 12h;Inert atmosphere; | General procedure: In a pressure tube 2 (0.525 mmol), K3PO4 (2.0 equiv), Pd(PPh3)4(3.0 mol%), and arylboronic acid (1.2 equiv) were mixed withdry 1,4-dioxane, degassed with argon und stirred for 12 h at60 C. After cooling to r.t., the solution was filtered throughCelite, washed with CH2Cl2, and the filtrate was concentrated byreduced pressure. The residue was purified by column chromatographyto receive the monosubstituted fluorenone 5a-h ingood yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 24h;Inert atmosphere; | General procedure: To a mixture of 2,2-dimethyl-6,7-ditriflyloxychroman-4-one(150 mg, 0.318 mmol), K3PO4 (202 mg, 0,95 mmol), and boronic acid (0.70 mmol) in dry 1,4-dioxane (4 mL) was added Pd(PPh3)4 (22 mg, 0.019 mmol) in a dried pressure tube under argon. The reaction mixture was stirred and heated in an aluminium heating block. The solvent was evaporated in vacuum, and the solid mixture was submitted to adsorptive filtration on silicagel using acetone as eluent removing the inorganic compounds. Silica was added to the solution, the acetone was evaporated,and the mixture was purified by column chromatography (eluent:heptane-EtOAc, the ratio is given below) giving the diarylated product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 60℃; for 5h;Inert atmosphere; | General procedure: To a mixture of 2,2-dimethyl-6,7-ditriflyloxychroman-4-one(150 mg, 0.318 mmol), K3PO4 (135 mg, 0,64 mmol), and boronic acid (0.349 mmol) in dry 1,4-dioxane (4 mL) was added Pd(PPh3)4 (11 mg, 0.0095 mmol) in a dried pressure tube under argon. The reaction mixture was stirred and heated in an aluminium heating block. The solvent was evaporated in vacuum,then the solid mixture was submitted to adsorptive filtration on silica gel using acetone as eluent removing the inorganic compounds. Silica was added to the solution, the acetone was evaporated,and the mixture was purified by column chromatography(eluent: heptane-EtOAc mixture, the ratio is given below) giving the monosubsituted product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; copper diacetate; In dichloromethane; at 20℃; for 12h;Molecular sieve; | General procedure: To a stirred solution of4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-n-propylphenol (18) (1.46g, 4.2 mmol) in CH2Cl2 (42 mL) was added molecular sieves4A (3.00 g), (3-formylphenyl)bronic acid (23a)(1.28 g, 8.4 mmol), copper acetate (II) (917 mg, 5.1 mmol) and pyridine (1.7 mL,21 mmol) at room temperature. The reaction mixture was stirred at sametemperature for 12 h. The reaction mixture was filtered through a pad of Celiteand rinsed with CHCl3. The filtrate was concentrated in vacuo. The residue was purified bysilica gel column chromatography (n-hexane/EtOAc= 10/1) to give the title compound (1.79 g, 95%) as a colorless oil; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; dichloromethane; for 5h;Inert atmosphere; Reflux; | 2.2.2 FeGm3(B3-C6H4CH = CH2)2 This complex was obtained like the previous one except that <strong>[15016-43-0]3-vinylphenylboronic acid</strong> (0.12 g, 0.81 mmol) was used instead of 4-vinylphenylboronic acid; the reflux time was prolonged to 50 h. Yield: 0.160 g (80%). Found (%): C, 49.46; H, 3.81; N, 14.75. Calc. for C22H20N6O6B2Fe (%): C, 48.76; H, 3.72; N, 15.51. MS(MALDI-TOF): m/z: 541 [M]+?. 1H NMR (DMSO-d6, delta, ppm): 5.28-5.85 (m, 4H, CH2(Vinyl)); 6.73 (m, 2H, HC(Vinyl)); 7.30 (m, 4H, orto-Ar); 7.44 (m, 2H, meta-Ar); 7.48 (m, 2H, para-Ar); 8.26 (s, 6H, HC = N). 13C{1H} NMR (DMSO-d6, delta, ppm): 113.81 (s, CH2 (Vinyl)); 127.95 (s, Ar); 130.04 (s, Ar); 136.23 (s, HC(Vinyl)); 137.82 (s, Ar); 143.59 (s, HC = N). IR (?Br), nu/cm-1 : 1552 nu(C=N), 901, 995-1004 m, 1138 nu(N-O), 1170 m nu(B-O), 1630 m nu(C=C). UV-vis (CH2Cl2): lambdamax, nm (epsilon · 10-3, mol-1 L cm-1): 248 (42), 277 (3.8), 284 (8.7), 293 (12), 305 (7.0), 324 (2.9), 415 (5.4), 438 (9.0). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; | Example 126A 6-(3-ethenylphenyl)-5-methylpyridin-2-amine (3-vinylphenyl)boronic acid (0.125 g, 0.845 mmol), <strong>[442129-37-5]6-chloro-5-methylpyridin-2-amine</strong> (0.129 g, 0.904 mmol), PdCl2dppf (0.043 g, 0.059 mmol), and potassium carbonate (0.269 g, 1.943 mmol) in dimethoxyethane (2.3 mL) and water (1.2 mL) were heated at 80 C. overnight. The mixture was diluted with ethyl acetate (20 mL) and washed with water (3*5 mL) and brine (5 mL) sequentially. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0 to 50% ethyl acetate-heptanes to afford the title compound as a colorless oil, (0.107 g, 60%). 1H NMR (500 MHz, DMSO-d6) delta 7.55-7.26 (m, 5H), 6.85-6.72 (m, 1H), 6.39 (d, J=8.3 Hz, 1H), 5.91-5.80 (m, 1H), 5.72 (s, 2H), 5.32-5.23 (m, 1H), 2.11 (s, 3H). MS (DCI+) m/z 211.0 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With sodium carbonate; palladium dichloride; In water; toluene; at 50℃; for 4h; | In a 250 mL three-necked flask, 21.4 g (0.1 mol) of 9-chloroacridine, 20.7 g (0.14 mol) of <strong>[15016-43-0]3-vinylphenylboronic acid</strong>, 0.12 g of PdCl2 catalyst, 100 g of toluene, 2 g of potassium carbonate, and 18 g of deionized water were sequentially added. , Heating to 50 C, reacting for 4 hours, cooling to 25 C, removing the solvent by rotary evaporation, adding 100g of methanol to wash and disperse, suction filtration to obtain a crude product, refining the crude product with 80g toluene, and drying to obtain 27.1g of the product, a yield of 96.5%, HPLC The content is 99.58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h;Inert atmosphere; | Under the protection of nitrogen, 1.3 g of compound D, 0.8 g of <strong>[15016-43-0]3-vinylbenzeneboronic acid</strong>, 0.2 g of tetrakis(triphenylphosphine) palladium, 2.4 g of K2CO3, 60 mL of tetrahydrofuran and 40 mL of water were heated to 80 C for 12h. After removing tetrahydrofuran using a rotary evaporator, water was added, extracted with dichloromethane, the liquid was separated and the organic phase was collected. Most of the solvent was removed with a rotary evaporator, neutral alumina was used as the stationary phase, petroleum ether was used as the eluent, the mixture was separated by column chromatography, and recrystallized from methanol to obtain a white solid G 0.96 g with a yield of 82%. |
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